Communication applications, such as email applications, allow users to share files by attaching them to a correspondence. However, the attachment process is typically a mechanical and limited process, where the user is given an option to browse through their computer and select a file to attach without providing any contextual information about the file, let alone any automatic suggestions based on contextual information. Furthermore, conventional systems are limited to attachment of local or network drive stored files, and every recipient intended to receive the correspondence may also receive the attachment regardless of whether the recipient has previously received the files. Moreover, the attachment process does not allow a user to configure permissions or set permissions based on other rules. Finally, conventional attachment processes are typically menu based and are not optimized for touch or gesture input mechanisms.